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Loring A. Chase and Oliver Chapman were the entrepreneurs who decided to develop the area into a resort community for “northern men of means.” A newspaper article called Chapman “cool, quiet, level-headed and judicial in his makeup, but once his mind is made up, he never relaxes his grip until his end is accomplished.” Chase, however, was described as “a rustler, quick to grasp, vigorous to act and relentless in his efforts.” sizable tract, including a large part of the Mizell homestead, and began selling lots to fellow Chicagoans. The following year, Phelps built his own home, a rambling cracker farmhouse in the midst of a 60-acre orange grove hugging the shores of Lake Osceola. Interestingly, part of the Phelps home survives as a wing of the Queen Anne-style Comstock-Harris House, otherwise known as Eastbank, which was built in 1883 by William Comstock, a wealthy grain merchant who also hailed from the Windy City. NORTHERN EXPOSURE The 1880s were pivotal years, and saw the reshaping of a haphazard frontier settlement into what today would be called a master-planned community. A major catalyst was completion in 1880 of the South Florida Railroad, which connected Sanford with Orlando — passing through what would become Winter Park — and later continuing to Tampa and the Gulf of Mexico. Loring Chase, a New Hampshire native who was raised in Massachusetts and lived in Chicago, first made his way to Central Florida by train. Harsh winters didn’t agree with the hard-working real estate broker, whose doctors had advised him to seek a warmer climate to alleviate his chronic respiratory problems. Chase, who visited the area in February 1881, was particularly smitten by the land surrounding lakes Osceola and Virginia. “Never will the delightful impression of that first visit be obliterated from my mind,” he recalled in a speech 10 years later. “Before me lay these beautiful rolling plains, covered everywhere by majestic pines, forming, not an impenetrable forest but a vast 46 LIVING IN WINTER PARK grove through which we could drive our team at will.” The land, although beautiful, was basically wilderness. “Save two faint streaks of iron, over which a boxcar went slowly once a day between Sanford and Orlando, and a rude platform and two or three windowless cabins of the original homesteaders, no sign of civilization greeted the eye,” Chase recalled. Still, once a real estate man, always a real estate man. Where some saw wilderness, Chase saw a winter resort for wealthy Northerners. “The idea of a town … on this delightful spot took full possession of me,” he said. Chase believed his boyhood friend, Oliver Chapman, would be an ideal partner in such a venture. Chapman, a Massachusetts-born importer of luxury goods, had moved to Florida in 1880 and lived in Sorrento, a small settlement in what’s now Lake County. The pair met in Sanford and set out to visit the property, which was then owned by B.R. Swoope, superintendent of the South Florida Railroad. Chapman, like Chase, recognized an opportunity when he saw it. By July 1881, they had bought 600 acres between present-day lakes Maitland, Virginia, Killarney and Osceola. The cost: $13,000 — the equivalent of about $290,000 today. Then, while in the vicinity, they sought validation from none other than Phelps, who had already �������������������������������������������������������������������������������������� ������������������������������������������������������������������ issued to shareholders of the Winter Park Company, which developed most of original Winter Park. enjoyed success marketing the area to out-of-staters. Phelps, who undoubtedly saw in Chase and Chapman an opportunity to increase the value of his own investments, could hardly have been more enthusiastic and encouraging. He claimed that, prior to relocating to Central Florida, he was “nearly dead with bronchitis of 30 years standing” as a result of living in New York, Ohio and Illinois. DIGITAL ART BY CHIP WESTON


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